Water → 5-Azido-5-(2-methoxyphenyl)-1-pentene

Participants

Reaction Steps

To a solution of crude 5-hydroxyl-5-(2-methoxyphenyl)-1-pentene, prepared as described above, in toluene (150 mL) at 0° to 40° C. was added diphenylphosphoryl azide (25.86 mL, 120 mmol) followed by DBU (17.95 mL, 120 mmol) and the resulting reaction mixture was stirred at room temperature (20° C. to 25° C.) for 28 hours. H2O was added, the aqueous layer was extracted with ether (x4), and the combined organic layers were washed with H2O (x2), 0.5N HCl (x2) and brine (x2), dried over MgSO4 and evaporated in vacuao. The crude product was purified by silica gel flash chromatography (5% EtOAc-95% hexanes) to provide the title compound as a colorless liquid (14 g). 1H NMR (CDCl3, 400 MHz) δ: 6.8-7.4 (4H), 5.8 (1H) (2H), 3.83 (3H, OMe), 1.8-2.2 (4H), 5.0

Provenance & Evidence